metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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catena-Poly[[bis­­[(2-carb­oxy­benzoato-κO)silver(I)](AgAg)]bis­­(μ-isonicotinic acid-κ2N:O)]

aInstitute of Marine Materials and Engineering, Shanghai Maritime University, Shanghai 200135, People's Republic of China
*Correspondence e-mail: lxf_shmtu@yahoo.com.cn

(Received 20 February 2008; accepted 7 April 2008; online 7 May 2008)

The title compound, [Ag(C8H5O4)(C6H5NO2)]n, contains one AgI atom, one phthalate ligand and one isonicotinic acid mol­ecule in the asymmetric unit. Each Ag atom is three-coordinated in a T-shaped geometry by two O atoms and one N atom from one phthalate ligand and two isonicotinic acid ligands. The isonicotinic acid ligand bridges two Ag atoms, forming a one-dimensional chain. Adjacent chains are linked by Ag—Ag inter­actions, leading to a double-chain. These double-chains are further linked via hydrogen bonds into a two-dimensional layer.

Related literature

For related literature, see: He et al. (2007[He, Y.-K., Han, Z.-B., Ma, Y. & Zhang, X.-D. (2007). Inorg. Chem. Commun. 10, 829-832.]); Xie et al. (2005[Xie, F.-T., Bie, H.-Y., Duan, L.-M., Li, G.-H., Zhang, X. & Xu, J.-Q. (2005). J. Solid State Chem. 178, 2858-2866.]).

[Scheme 1]

Experimental

Crystal data
  • [Ag(C8H5O4)(C6H5NO2)]

  • Mr = 396.10

  • Monoclinic, C 2/c

  • a = 13.540 (3) Å

  • b = 8.160 (2) Å

  • c = 24.223 (5) Å

  • β = 99.546 (15)°

  • V = 2639 (1) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.56 mm−1

  • T = 293 (2) K

  • 0.37 × 0.32 × 0.27 mm

Data collection
  • Siemens P4 four-circle diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.597, Tmax = 0.680

  • 3909 measured reflections

  • 3037 independent reflections

  • 1879 reflections with I > 2σ(I)

  • Rint = 0.034

  • 3 standard reflections every 97 reflections intensity decay: 1.0%

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.119

  • S = 1.00

  • 3037 reflections

  • 199 parameters

  • H-atom parameters constrained

  • Δρmax = 0.99 e Å−3

  • Δρmin = −0.71 e Å−3

Table 1
Selected geometric parameters (Å, °)

Ag1—N1 2.179 (4)
Ag1—O3 2.185 (3)
Ag1—O2i 2.621 (3)
Ag1—Ag1ii 3.2123 (11)
N1—Ag1—O3 164.57 (14)
N1—Ag1—O2i 93.52 (12)
O3—Ag1—O2i 101.74 (11)
Symmetry codes: (i) x, y-1, z; (ii) [-x+1, y, -z+{\script{3\over 2}}].

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯O6iii 0.82 1.80 2.616 (5) 175
O5—H5A⋯O4 0.82 1.57 2.390 (5) 180
Symmetry code: (iii) [x, -y+1, z-{\script{1\over 2}}].

Data collection: XSCANS (Siemens, 1994[Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Comment top

Silver ion reacts with isonicotinic acid and imidazole under hydrothermal conditions to form [Ag8(in)6(NO3)2] and [Ag(in)(Hin)]0.5[Ag(in)] (Hin = isonicotinic acid) (Xie et al., 2005). With phthalic acid in place of imidazole, the reaction yields the title compound.

In the title compound, the AgI atom is three-coordinated by two O atoms and one N atom from one phthalate ligand and two isonicotinic acid ligands in a T-like geometry, with an O—Ag—N bond angle being 164.57 (14)° (Fig. 1; Table 1), giving a chain structure. Furthermore, the adjacent chains are linked by Ag···Ag interactions (He et al., 2007) to form a one-dimensional double-chain (Fig. 2). These double-chains are further linked via O—H···O hydrogen bonds (Table 2) into a two-dimensional layer. The hydrogen bonding interactions enhance the stability of the complex.

Related literature top

For related literature, see: He et al. (2007); Xie et al. (2005).

Experimental top

A mixture of Ag(NO3) (0.085 g, 0.5 mmol), isonicotinic acid (0.123 g, 1 mmol), phthalic acid (0.166 g, 1 mmol) and water (10 ml) was sealed in a 23 ml Teflon-lined reactor, which was heated at 473 K for 4 d and then cooled to room temperature at a rate of 5 K h-1 (yield 72%). Analysis calculated for C14H10AgNO6: C 42.45, H 2.54, N 3.54%; found: C 42.39, H 2.61, N 3.48%.

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 and O—H = 0.82Å and Uiso(H) = 1.2Ueq(C,O).

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: XSCANS (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. The coordination geometry of the Ag atom in the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) x, -1 + y, z.]
[Figure 2] Fig. 2. The one-dimensional double-chain connected by Ag···Ag interactions.
catena-Poly[[bis[(2-carboxybenzoato-κO)silver(I)](Ag—Ag)]bis(µ-isonicotinic acid-κ2N:O)] top
Crystal data top
[Ag(C8H5O4)(C6H5NO2)]F(000) = 1568
Mr = 396.10Dx = 1.994 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 28 reflections
a = 13.540 (3) Åθ = 5.2–12.4°
b = 8.160 (2) ŵ = 1.56 mm1
c = 24.223 (5) ÅT = 293 K
β = 99.546 (15)°Block, purple
V = 2639 (1) Å30.37 × 0.32 × 0.27 mm
Z = 8
Data collection top
Siemens P4 four-circle
diffractometer
1879 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 27.5°, θmin = 1.7°
ω–2θ scansh = 171
Absorption correction: ψ scan
(North et al., 1968)
k = 110
Tmin = 0.597, Tmax = 0.680l = 3131
3909 measured reflections3 standard reflections every 97 reflections
3037 independent reflections intensity decay: 1.0%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0526P)2]
where P = (Fo2 + 2Fc2)/3
3037 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.99 e Å3
0 restraintsΔρmin = 0.72 e Å3
Crystal data top
[Ag(C8H5O4)(C6H5NO2)]V = 2639 (1) Å3
Mr = 396.10Z = 8
Monoclinic, C2/cMo Kα radiation
a = 13.540 (3) ŵ = 1.56 mm1
b = 8.160 (2) ÅT = 293 K
c = 24.223 (5) Å0.37 × 0.32 × 0.27 mm
β = 99.546 (15)°
Data collection top
Siemens P4 four-circle
diffractometer
1879 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.034
Tmin = 0.597, Tmax = 0.6803 standard reflections every 97 reflections
3909 measured reflections intensity decay: 1.0%
3037 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.00Δρmax = 0.99 e Å3
3037 reflectionsΔρmin = 0.72 e Å3
199 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.40822 (3)0.04719 (5)0.698630 (15)0.05417 (17)
C10.4164 (4)0.7535 (6)0.58243 (19)0.0405 (11)
C20.4211 (3)0.5872 (5)0.60835 (17)0.0347 (10)
C30.4339 (4)0.4453 (6)0.57882 (17)0.0397 (10)
H3A0.44170.45140.54150.048*
C40.4348 (4)0.2962 (6)0.60478 (18)0.0413 (11)
H4A0.44300.20200.58440.050*
C50.4137 (4)0.4183 (6)0.68640 (19)0.0442 (12)
H5B0.40700.40870.72390.053*
C60.4119 (4)0.5724 (6)0.66396 (19)0.0455 (12)
H6A0.40460.66440.68560.055*
C70.3575 (4)0.0952 (6)0.80056 (17)0.0383 (11)
C80.3373 (3)0.2215 (5)0.84252 (16)0.0307 (9)
C90.3225 (3)0.3796 (6)0.82196 (17)0.0368 (10)
H9A0.32400.39750.78420.044*
C100.3056 (4)0.5119 (6)0.8547 (2)0.0437 (11)
H10A0.29580.61640.83940.052*
C110.3036 (4)0.4842 (6)0.9109 (2)0.0453 (12)
H11A0.29270.57110.93400.054*
C120.3177 (4)0.3304 (6)0.93258 (18)0.0403 (11)
H12A0.31590.31450.97040.048*
C130.3346 (3)0.1963 (5)0.89994 (17)0.0321 (9)
C140.3497 (4)0.0355 (6)0.93203 (18)0.0411 (11)
N10.4245 (3)0.2820 (5)0.65827 (15)0.0414 (9)
O10.3992 (3)0.7496 (5)0.52779 (12)0.0626 (11)
H1A0.38960.84310.51560.094*
O20.4267 (3)0.8778 (4)0.60899 (13)0.0513 (9)
O30.3817 (3)0.1459 (4)0.75691 (13)0.0579 (10)
O40.3483 (3)0.0565 (4)0.80925 (14)0.0619 (11)
O50.3438 (3)0.1015 (4)0.90631 (14)0.0579 (10)
H5A0.34540.08580.87300.087*
O60.3672 (3)0.0408 (4)0.98320 (13)0.0641 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0797 (3)0.0432 (2)0.0430 (2)0.0001 (2)0.02032 (19)0.01176 (18)
C10.046 (3)0.038 (3)0.037 (2)0.002 (2)0.007 (2)0.002 (2)
C20.037 (2)0.037 (2)0.030 (2)0.001 (2)0.0055 (18)0.0028 (18)
C30.055 (3)0.036 (2)0.028 (2)0.003 (2)0.008 (2)0.0023 (19)
C40.055 (3)0.037 (2)0.034 (2)0.000 (2)0.012 (2)0.0002 (19)
C50.061 (3)0.039 (3)0.034 (2)0.002 (2)0.012 (2)0.0022 (19)
C60.065 (3)0.042 (3)0.031 (2)0.005 (3)0.014 (2)0.002 (2)
C70.046 (3)0.042 (3)0.027 (2)0.001 (2)0.0060 (19)0.0026 (19)
C80.038 (2)0.028 (2)0.0250 (18)0.0007 (19)0.0035 (17)0.0007 (17)
C90.050 (3)0.034 (2)0.0278 (19)0.001 (2)0.0098 (19)0.0021 (18)
C100.045 (3)0.027 (2)0.057 (3)0.003 (2)0.004 (2)0.001 (2)
C110.058 (3)0.037 (3)0.042 (2)0.005 (2)0.009 (2)0.010 (2)
C120.051 (3)0.040 (3)0.030 (2)0.003 (2)0.007 (2)0.0033 (19)
C130.038 (2)0.028 (2)0.031 (2)0.002 (2)0.0056 (18)0.0000 (17)
C140.053 (3)0.036 (3)0.035 (2)0.004 (2)0.012 (2)0.006 (2)
N10.053 (2)0.038 (2)0.0349 (18)0.0020 (19)0.0101 (18)0.0034 (17)
O10.112 (3)0.042 (2)0.0295 (16)0.002 (2)0.0001 (19)0.0104 (15)
O20.075 (3)0.0364 (18)0.0425 (18)0.0043 (19)0.0082 (17)0.0005 (16)
O30.101 (3)0.0417 (19)0.0379 (17)0.004 (2)0.0313 (19)0.0044 (16)
O40.116 (3)0.0339 (18)0.0379 (17)0.003 (2)0.019 (2)0.0053 (15)
O50.107 (3)0.0303 (17)0.0380 (17)0.006 (2)0.017 (2)0.0037 (15)
O60.117 (3)0.047 (2)0.0278 (15)0.004 (2)0.0086 (19)0.0078 (16)
Geometric parameters (Å, º) top
Ag1—N12.179 (4)C7—O41.265 (6)
Ag1—O32.185 (3)C7—C81.504 (6)
Ag1—O2i2.621 (3)C8—C91.385 (6)
Ag1—Ag1ii3.2123 (11)C8—C131.412 (5)
C1—O21.197 (6)C9—C101.380 (6)
C1—O11.306 (5)C9—H9A0.9300
C1—C21.492 (6)C10—C111.387 (7)
C2—C61.379 (6)C10—H10A0.9300
C2—C31.386 (6)C11—C121.361 (7)
C3—C41.368 (6)C11—H11A0.9300
C3—H3A0.9300C12—C131.391 (6)
C4—N11.331 (5)C12—H12A0.9300
C4—H4A0.9300C13—C141.521 (6)
C5—N11.325 (6)C14—O61.223 (5)
C5—C61.368 (7)C14—O51.276 (6)
C5—H5B0.9300O1—H1A0.8200
C6—H6A0.9300O5—H5A0.8200
C7—O31.229 (5)
N1—Ag1—O3164.57 (14)C9—C8—C7115.3 (3)
N1—Ag1—O2i93.52 (12)C13—C8—C7127.1 (4)
O3—Ag1—O2i101.74 (11)C10—C9—C8123.4 (4)
N1—Ag1—Ag1ii102.98 (11)C10—C9—H9A118.3
O3—Ag1—Ag1ii71.85 (11)C8—C9—H9A118.3
O2—C1—O1123.4 (4)C9—C10—C11117.9 (4)
O2—C1—C2123.5 (4)C9—C10—H10A121.0
O1—C1—C2113.1 (4)C11—C10—H10A121.0
C6—C2—C3118.0 (4)C12—C11—C10120.3 (4)
C6—C2—C1119.1 (4)C12—C11—H11A119.8
C3—C2—C1122.9 (4)C10—C11—H11A119.8
C4—C3—C2119.8 (4)C11—C12—C13122.2 (4)
C4—C3—H3A120.1C11—C12—H12A118.9
C2—C3—H3A120.1C13—C12—H12A118.9
N1—C4—C3122.0 (4)C12—C13—C8118.6 (4)
N1—C4—H4A119.0C12—C13—C14114.1 (4)
C3—C4—H4A119.0C8—C13—C14127.3 (4)
N1—C5—C6124.3 (4)O6—C14—O5120.8 (4)
N1—C5—H5B117.9O6—C14—C13118.3 (4)
C6—C5—H5B117.9O5—C14—C13120.9 (4)
C5—C6—C2118.0 (5)C5—N1—C4117.8 (4)
C5—C6—H6A121.0C5—N1—Ag1118.6 (3)
C2—C6—H6A121.0C4—N1—Ag1123.3 (3)
O3—C7—O4121.4 (4)C1—O1—H1A109.5
O3—C7—C8117.0 (4)C7—O3—Ag1114.1 (3)
O4—C7—C8121.6 (4)C14—O5—H5A109.5
C9—C8—C13117.6 (4)
O2—C1—C2—C616.8 (8)C9—C8—C13—C120.2 (7)
O1—C1—C2—C6162.7 (4)C7—C8—C13—C12178.0 (4)
O2—C1—C2—C3163.7 (5)C9—C8—C13—C14179.3 (4)
O1—C1—C2—C316.8 (7)C7—C8—C13—C141.1 (8)
C6—C2—C3—C41.3 (7)C12—C13—C14—O615.3 (7)
C1—C2—C3—C4178.2 (5)C8—C13—C14—O6163.8 (5)
C2—C3—C4—N10.5 (8)C12—C13—C14—O5164.4 (5)
N1—C5—C6—C20.4 (8)C8—C13—C14—O516.5 (8)
C3—C2—C6—C51.3 (7)C6—C5—N1—C40.4 (8)
C1—C2—C6—C5178.3 (5)C6—C5—N1—Ag1173.0 (4)
O3—C7—C8—C916.1 (6)C3—C4—N1—C50.4 (7)
O4—C7—C8—C9162.6 (5)C3—C4—N1—Ag1172.6 (4)
O3—C7—C8—C13162.1 (5)O3—Ag1—N1—C54.1 (8)
O4—C7—C8—C1319.2 (8)Ag1ii—Ag1—N1—C564.4 (4)
C13—C8—C9—C100.1 (7)O3—Ag1—N1—C4168.9 (5)
C7—C8—C9—C10178.3 (4)Ag1ii—Ag1—N1—C4122.6 (4)
C8—C9—C10—C110.1 (8)O4—C7—O3—Ag10.9 (6)
C9—C10—C11—C120.3 (8)C8—C7—O3—Ag1179.6 (3)
C10—C11—C12—C130.2 (8)N1—Ag1—O3—C70.2 (8)
C11—C12—C13—C80.1 (7)Ag1ii—Ag1—O3—C772.7 (4)
C11—C12—C13—C14179.3 (5)
Symmetry codes: (i) x, y1, z; (ii) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O6iii0.821.802.616 (5)175
O5—H5A···O40.821.572.390 (5)180
Symmetry code: (iii) x, y+1, z1/2.

Experimental details

Crystal data
Chemical formula[Ag(C8H5O4)(C6H5NO2)]
Mr396.10
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)13.540 (3), 8.160 (2), 24.223 (5)
β (°) 99.546 (15)
V3)2639 (1)
Z8
Radiation typeMo Kα
µ (mm1)1.56
Crystal size (mm)0.37 × 0.32 × 0.27
Data collection
DiffractometerSiemens P4 four-circle
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.597, 0.680
No. of measured, independent and
observed [I > 2σ(I)] reflections
3909, 3037, 1879
Rint0.034
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.119, 1.00
No. of reflections3037
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.99, 0.72

Computer programs: XSCANS (Siemens, 1994), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected geometric parameters (Å, º) top
Ag1—N12.179 (4)Ag1—O2i2.621 (3)
Ag1—O32.185 (3)Ag1—Ag1ii3.2123 (11)
N1—Ag1—O3164.57 (14)O3—Ag1—O2i101.74 (11)
N1—Ag1—O2i93.52 (12)
Symmetry codes: (i) x, y1, z; (ii) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O6iii0.821.802.616 (5)175
O5—H5A···O40.821.572.390 (5)180
Symmetry code: (iii) x, y+1, z1/2.
 

Acknowledgements

The authors thank Shanghai Maritime University for supporting this work.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationHe, Y.-K., Han, Z.-B., Ma, Y. & Zhang, X.-D. (2007). Inorg. Chem. Commun. 10, 829–832.  Web of Science CSD CrossRef CAS Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar
First citationXie, F.-T., Bie, H.-Y., Duan, L.-M., Li, G.-H., Zhang, X. & Xu, J.-Q. (2005). J. Solid State Chem. 178, 2858–2866.  Web of Science CSD CrossRef CAS Google Scholar

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